Sort by
Relevancy

Free Stories

100%
Traci the Maid
Traci had gotten a job as a maid in a rich man's house. She looked just like any blond 26-year old woman - long legs, slender waist and high size C breasts. She had a heart-shaped face and giggled at all the right times. Only Traci had a secret that nobody at her knew job knew about - she had a 6&qu... Read full Story
shemale lover 2013-07-19 5,369 Stockings Cumshot blonde Uniform Guy Fucks Shemale
50%
Healthy Behavior
"Uhh…is Mr. Stanford around?" "One moment dear…ooh, damn heels. Makes it impossible to walk through doorways. Here I am ma'am. So, did the maid get you here alright? Hello? Earth to…" "I can't believe this…" "Oh, the heels? Yeah... Read full Story
shemale lover 2011-10-19 3,956 Big Tits transsexual oral
100%
Just One of Those Days Part 2
Hello again. My name is Amanda, though sometimes I use the shortened version Mandy, when the mood suits me. I'm 33 and have stayed single for three years, since I discovered that Richard, my boyfriend, was not only cheating on me with dozens of women, some my so called friends but was al... Read full Story
shemale lover 2011-12-09 3,242 cum massage shemale sex
89%
Fem Firm 2 -The Weathergirl
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2016-11-14 18,021 big dick anal sex suck Blowjob cock sucking workplace
100%
Meeting Amanda Ch. 2 - The Next Day
After a hot evening together, the story continues https://www.ashemaletube.com/story/meeting-amanda-6595/ ------------------------------------------------------------------------------------------------------------- “I could really use a shower,” Amanda said while she... Read full Story
rforasht 2022-09-07 4,313 Masturbation Shemale and Girl redhead Guy Fucks Shemale cum eating anal creampie couple & shemale
45%
Shemale Prostate Orgasmic Bliss!!!!
if she wanted breasts." "Oh no. That's the amazing part. The more I dressed him the more feminine he became. By now I'd moved him her and her clothes into the other bedroom. She wasn't happy with that but we came to an agreement; I'd milk her once a week and she... Read full Story
ProstateMilker 2015-05-01 13,819 Masturbation cum orgasm cumshots prostate
100%
My Noisy Upstairs Neighbors
So... I just moved into my new apartment a few weeks ago, and ever since then all day every day I have been hearing loud noises from my upstairs neighbors. Not just normal walking-around noise, but loud and heavy bangs, crashes, and poundings against the floor, my ceiling. Not only was the sound ann... Read full Story
Chrissy Tunnell 2024-07-15 1,316 Crossdresser Bareback Fetish Blowjob Ladyboy gangbang domination Guy Fucks Shemale sissy double anal
91%
Panty Town
Chapter One -- Jamie Jamie Sanders did not think he was a sissy. Growing up, he played with trucks and showed his innate male aggression though soldiers games with the other boys. He climbed trees and watched baseball with his Dad and brother. Unfortunately, by the time he was in eighth grad... Read full Story
shemale lover 2012-01-29 19,396 Big Tits sucking ass licking fucking
75%
Backsliding: Tim's Story
Every man has a weakness, but not everyman knows what that weakness is until it is too late. The story I'm about to tell is something I'm not entirely proud of. My name is Tim. I'm a 22-year-old college student at California State University. I'm almost at the end of my senior year studying to be... Read full Story
shemale lover 2012-02-09 4,947 sucking fingering Guy Fucks Shemale
76%
Porn Princess
They say if you are going on a journey of revenge, to dig 2 graves, one for your enemy and one for yourself. I thought I understood the meaning of that saying, but never so much as right now. My name is Dan, and at the age of 21, I had been working for nearly 2 years as a production manager for ... Read full Story
shemale lover 2012-09-02 23,980 Cumshot Blowjob fuck fingering big boobs
100%
The Society
I met her during the summer. I was only nineteen and working to save some money for college. I had been raised by my grandparents who had both passed away over the past year. After the burial costs I was far from wealthy. My parents weren't around so I was on my own at a young age. I had moved a cou... Read full Story
shemale lover 2013-01-10 17,317 Crossdresser sucking Big Cock ass licking big boobs
85%
THE WEATHERGIRL BY B-MAN
PART 1: A COURTESY CLIENT BLOWJOB Three weeks into my gig at Coxon & Dicster had been a blast. At first, a few of the girls had some reservations about me working there because I wasn't transgendered myself but I guess I won them over with my naturally cheerful personality. At least,... Read full Story
bennyx709 2015-07-29 7,526 Crossdresser hardcore ass fucking cd
97%
FEM FIRM 4-POP SECRET
Fem Firm 4: Pop Secret by: B-Man View Story Details Rating: XXXAdd Review Added: 11/20/2016 Complete:no Synopsis: Ruby learns a family secret which will change her life forever. Categories:Bimbo Workplace Situations Keywords:Long Finger Na... Read full Story
bennyx709 2016-11-22 10,002 anal sex cocksucking workplace situations
80%
Too Much Hospitality
Ash looked himself over in his bedroom mirror critically, finding himself oddly self-conscious about his looks. He had been texting Laura all throughout the day and they had agreed that dressing pretty casual would draw the least suspicion, so he had. He wore a simple patterned t-shirt and some ... Read full Story
ASSEaster5678 2018-09-17 8,687 anal Blowjob transsexual oral sex cum swallowing romance transgendered Consensual Sex Older Female / Males
100%
ROBERTO’S SECRET by Spanky De Bautumn
Cody Daniels was only trying to help her country; she never dreamed things would come to this. She was patriotic and felt compelled to do whatever asked of her to aid in the capture of the terrorist known only as "Roberto". But lying in his bed, bound and gagged, Cody wondered why she let herself go... Read full Story
SpankydeBautumn 2021-01-22 4,905 Crossdresser Cumshot Creampie Fetish domination Guy Fucks Shemale
100%
How I Became Chrissy the Caged Sissy
I am a sissy, or femboy, or tgurl, or shemale? Well either way I like wearing female clothes and being treated like a girl, especially in the bedroom, and now I also like being locked up in a chastity cage that I wear 24/7 now. This is the story of how I became a caged sissy: "Put it on and ... Read full Story
Chrissy Tunnell 2022-01-27 4,173 Crossdresser solo Amateur Masturbation Fetish Blowjob Ladyboy domination Guy Fucks Shemale Sex Toys Mature Homemade
50%
A LA DÉCOUVERTE DE L'AMBRE ⚧️
J'ai toujours aimé la lingerie féminine. De regarder des catalogues à voir des copines le porter, j'ai adoré le look et la sensation de la lingerie sexy et soyeuse, mais pour moi, cela a toujours été plus profond. À 18 ans, j'ai essayé ma première paire de culottes, oh mon Dieu, c'était merveilleux ... Read full Story
Femboy 2021 2023-02-17 1,045 Stockings Crossdresser Cumshot Bareback Fetish Big Cock Lingerie Shemale and Girl domination Guy Fucks Shemale Sex Toys
100%
Vengeance is sweet
What a warm day. Really hot, perhaps even the camels fainted in the zoo because of the heat. The thermometer reached 35°C that day. At these temperatures people usually aren’t up to do anything. So did I, because I sat together with Claude in his front yard. We were both sitting on our bea... Read full Story
shemale lover 2011-09-04 4,551 anal shemales lesbian sex
71%
Glory Hole Girlfriend
My boyfriend likes to take me to the local adult bookstore, into the back where the video arcade is. There's always a lot of men there, strangers that we don't know, and I feel funny when they look at me. They wonder why a pretty young woman would be back there. It smells too. A rich sweaty sc... Read full Story
shemale lover 2011-12-18 7,344 Creampie ass fucking mouth fuck
85%
Transsexual Cheerleader
Transsexual Cheerleader Marcus, the football team quarterback, was well known at the university as the "most datable on campus", and he had had his share of women. From the nice virginly freshman, to the hottest senior whores. It was no wonder that he was so popular. 6'4, 240 pounds of pur... Read full Story
shemale lover 2012-05-13 3,834 anal sex Creampie Blowjob
100%
Fantasies Fulfilled
I enjoy crossdressing and do so when ever I can. About the only time I dress as a man is to go to work. I have been doing this since I was eleven years old. I love to have sex with a man as if I was a woman and really think I should have been born a girl. I think like a girl and naturally act like a... Read full Story
shemale lover 2012-05-26 4,333 anal sex Creampie Blowjob crossdressing
100%
Florida TG Experience
I had known Jan from High School, we always had an attraction for each other but were dating someone else or married at the time. Jan had actually married a friend of mine and I was envious of course. She at that time had sandy blonde hair, and a body to die for. One evening we had them over for dr... Read full Story
Jon Paul 2018-08-13 10,973 Group Sex Big Tits Bareback Creampie Blowjob blonde Asian Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth cum in mouth double anal
100%
Gemini Sluts and Gang
My good friend Renee and I had set up a double date gang bang for tonight now that she was finally out of the closet and ready. She has decided that life is too short to remain in the closet and miss out on all the fun. Renee and I have so much in common. Besides loving sex, we both have a fetish f... Read full Story
Regina10 2021-04-09 4,476 Group Sex Big Tits Cumshot Bareback Fetish Blowjob blonde gangbang Lingerie Guy Fucks Shemale Ass to Mouth cum in mouth
100%
Sissy Femboy Chrissy in Drag 2: At the Apartment
This is Part 2 to the article I wrote called "Sissy Femboy Chrissy in Drag at the Club." In that story I explained how I am 41 but look, feel and sound younger, that I shave myself smooth and like dressing in gurly panties and other female clothes to be a sissy femboy for older guys. A guy I met on ... Read full Story
Chrissy Tunnell 2022-02-03 3,613 Crossdresser Amateur Bareback Creampie Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature
75%
Passion in the Rough
Tonight, I was searching in vain for a parking place close to the club, but unfortunately, I had arrived late and there were no empty spaces close by. I drove around and went down several streets in the same block until I found an empty spot. That was perfect I thought as I found a parking place and... Read full Story
Regina10 2024-04-27 3,357 anal Crossdresser Big Tits Outdoor Bareback Creampie Blowjob blonde Big Cock Ladyboy gangbang Guy Fucks Shemale
57%
Angel The Vampire
Angel stood in the shadows watching hungrily as the group of laughing young college kids came toward her down the alley. The group was made up of four guys and a girl. The girl was hanging all over one of the guys and it screamed how badly she wanted to get in his pants. Angel's smile broadened with... Read full Story
shemale lover 2011-11-08 4,125 suck shemale
96%
Riding Home With Strangers
The music was running, the booze was flowing through my veins and I was not ready to leave just yet. My ride had to leave early, because my driver's hours were up, and I didn't want to force him. I didn't think I would be having so much fun before I came here. I met a group down here who li... Read full Story
shemale lover 2013-01-30 8,995 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
100%
Reshooting the Scene, Chapter 1
I have been a porn aficionado since I was a teenager. My first dabblings were with Hustler magazine and a *very* hardcore mini-novel called “Her Busted Asshole,” which told the raunchy story of Ginny Cummings’ sexual coming of age. In addition to the very graphic story, it had full color glossy p... Read full Story
Lovelace 2021-06-07 4,542 Bareback threesome Blowjob blonde Big Cock Sex Toys Ass to Mouth
100%
Santa & Mrs. Claus
In my story called "Santa Likes Fembois" here I explained that I discovered that last Christmas when Santa Claus visited my house then made me suck on his cock before fucking my boypussy. He also gave me an actual present: a winning lottery ticket. Well, with that multi-million dollar winning ticket... Read full Story
Chrissy Tunnell 2022-12-01 3,621 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy Lingerie domination Guy Fucks Shemale Mature cum in mouth
100%
The Terrace View Apartments Part 3
Standing alone on the street outside the Terrace View Apartment complex, I found myself shaking uncontrollably with a mixture of apprehension and excitement. Physical exhaustion probably had a lot to do with my nerves as well. After all, I’d only begun what I had hoped would be a new life a fe... Read full Story
shemale lover 2011-11-18 3,358 anal cum oral crossdressing
100%
Just One of Those Days
Let me start by introducing myself. My name is Amanda, though I sometimes use the shortened version Mandy. I am thirty-three but my sexual awakening didn't really occur until I had turned thirty. Previously I had been a generally shy and quiet girl with a steady and normal relationship. ... Read full Story
shemale lover 2011-12-07 4,778 shemale tattoo shaved
100%
Beefy Buns
It's hard to get good help. Probably, that's true in any business, but it's especially difficult to find decent employees in the fast food racket. Believe me; I've tried. I manage the local Beefy Buns franchise--burgers, fries, and shakes is our mainstay, but the menu also features fish and chick... Read full Story
shemale lover 2012-04-22 6,121 anal sex Creampie blonde shemale
50%
The Ultimate Cock Ball Torture
I miss my cock. Sometimes. I had one once - one of my very own, connected right to me - but now it's gone. Never thought I would miss it. I'm sure you've guessed by now that I am a full transexual. I had the boob job and started hormone treatment years ago and felt much better as a shemale th... Read full Story
shemale lover 2012-04-29 3,593 anal sex oral sex
50%
The Zodiac Coins: Libra
2400 YEARS AGO... He was a humble shepherd. It was night and the flocks were sleeping. As he gazed at the stars, he saw a shooting star. He knew it was a portent of some kind, but was not mystic enough to know what. A little while later he saw another shooting star and guessed that wha... Read full Story
shemale lover 2011-10-18 4,666 Group Sex Masturbation shemale oral
100%
A Fairy Tale Part 2
=-=-Chapter Six-=-= I woke up sometime later and I was feeling better, even a little hungry actually, and I wanted a shower and I needed to pee and...I cocked my head as I heard the unmistakable sounds of Mistress Stacy's bed moving. She had a large one, king sized, with old springs or somethi... Read full Story
shemale lover 2011-12-06 6,746 Creampie Big Cock ass fucking
100%
April Fools!!
I'm Jimmy James and I've been hanging out with the same six guys since we started college. We're a pretty close knit bunch and have stayed in touch since then. At 25, I'm the only one of the seven of us still not married. Even though we all still get together for parties and get togethers, for t... Read full Story
shemale lover 2012-01-04 11,399 anal oral cd
100%
Becoming A She-Males Bitch Part 2
After last nights ordeal I was given something to drink and taken to a bedroom upstairs. What I drank must have had some kind of drug in it because I was knocked out. I bet I was asleep in just a couple of minutes. I barely even remember lying down. When I woke up I was naked, sore as hell and fe... Read full Story
shemale lover 2012-01-04 8,845 cum oral domination
92%
T-Girl Meets T-Girl
It was a silent car ride home. He looked at her, she looked out the window. She looked at him, his eyes were on the road. Neither of them broke the silence. It stayed that way until he parked in her mom's driveway. The soft-spoken young man told his girlfriend, "Goodnight Ashley. I'll call y... Read full Story
shemale lover 2012-08-29 6,179 anal sex Cumshot shemale and shemale domination blondie
92%
A Surprise Relationship
This is a fictional story, although it is based on people I did know. "Tony" and his twin sister "Kim" are based on a set of twins I knew, who were almost identical. I did have a relationship with "Kim" for almost two years, however, the relationship with "Tony&quo... Read full Story
shemale lover 2013-01-29 5,323 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
80%
fuck by my best friend's family
= Part 1. Alice's father = My name is Onikky 28-year-old Shemale from ASIAN, this story only shares the first experience of making love. The story begins when I first moved to a big city, looking for a new atmosphere, I don't have a place to live that I know is only my friend's name Alice who ... Read full Story
Onikky 2019-06-25 9,398 Amateur Masturbation Big Cock Asian Ladyboy gangbang Lingerie domination Guy Fucks Shemale Sex Toys Homemade Ass to Mouth cum in mouth
91%
Masturbation fantasies: Amanda, queen of the peep show
A guy visits a peep show with unexpected results. As he gets to watch a girl with something special, he discovers his hidden desires. This story contains: peep show – voyeur – gloryhole - fake tits – group masturbation – male masturbation – shemale – frottage - titfucking When William finall... Read full Story
ThatEroticWriter 2019-07-24 8,478 Big Tits Cumshot Masturbation Uniform Frottage
100%
He Could Have R*ped Me!
This guy was so big, taller than me and I'm 6 feet, and bigger, not fat, just right for his big size, and I am so skinny, except for my tummy, that he could have pinned me down and forced himself onto and into me against my will, and no matter how much I'd struggle with him and fight back, he could ... Read full Story
Chrissy Tunnell 2022-02-02 2,796 Crossdresser Amateur Bareback Fetish Blowjob Ladyboy domination Guy Fucks Shemale Homemade cum in mouth
100%
Santa Likes Shemales Femboys
Did you know Santa Clause is real....and he likes shemales femboys??!I It happened last Christmas Eve. I fell asleep watching the snow fall just outside my window. I was comfy under my layers of warm blankets I clutched tightly, in the black lace panties and red lingerie night dress or nighty I wear... Read full Story
Chrissy Tunnell 2022-12-01 3,654 Small Tits Crossdresser Amateur Bareback Fetish Big Cock Ladyboy Lingerie domination Guy Fucks Shemale Mature
33%
Duel With the Devil, Chapter 20 of The Greatest Liar
Duel With The Devil This is a work of fiction. All characters (including the narrator), celebrities, places, residences, neighborhoods, restaurants, legal agreements and proceedings, events and incidents are either the products of the author's imagination or used in a fictitious manner. Any r... Read full Story
the greatest liar 2023-07-19 4,123 anal Bareback Creampie Ebony Guy Fucks Shemale post-op celebrity post op sex
50%
I Believe
I Believe I had just started my senior year in college and was in my 3rd year of transitioning from a male to a female. I couldn’t start in high school so when I graduated and I started college I started as Nikki. The first three years working on my communications degree I used to see people goin... Read full Story
ShelleyParker 2024-07-08 847 Bareback Big Cock Guy Fucks Shemale Interracial Ass to Mouth cum in mouth
91%
Lakeside Awakening
If anyone had told the way I’d meet my soul mate a few years ago, I never would have believed it. It was my senior year of high school and I had recently gotten out of yet another bad relationship with a girl. Lina had been a pretty, chubby blonde with a nice personality but a nasty temper. We... Read full Story
shemale lover 2011-06-27 7,452 ass Blowjob shemale
60%
The Ultimate Cock Ball Torture
I miss my cock. Sometimes. I had one once - one of my very own, connected right to me - but now it's gone. Never thought I would miss it. I'm sure you've guessed by now that I am a full transexual. I had the boob job and started hormone treatment years ago and felt much better as a shemale th... Read full Story
shemale lover 2011-11-12 7,093 shemale transformation
75%
Old Folks Part 2
It had been eleven months since that day when I arrived at Honey and Frank's house. It was about 1am at night as I stood in a quiet street waiting for Frank to pick me up. I had just finished with my last client for the night a good blowjob with him ending up cumming on my face. I was touching up my... Read full Story
shemale lover 2012-01-10 6,880 transsexuals erotica romance crossdressers
100%
Steve to Stephanie Chapter 1
This is my first attempt at a longer story with deeper characters and a more evolved story line. Stay tuned for the next chapter. As always comments are welcome. * Steve was mild mannered guy with a big secret. Steve was an avid cross dresser, very bi actually leaning towards being gay. Steve... Read full Story
shemale lover 2013-01-29 3,855 anal sex Cumshot Masturbation Blowjob Guy Fucks Shemale
90%
Lost Island
Bright light hit my eyes when I opened them after a long time. My mouth was full of sand, my toung dry and the taste of salt overwhelmed me. I was stranded. My boat sank in a terrible storm and my body was washed on this lonely beach of a tropical island. The sea was calm and there were almost no w... Read full Story
xgandalf 2016-05-04 6,340 sucking gangbang domination ass fuking Shemale on Guy
100%
The Girl Next Door Ch. 02
derezzed Chapter 2 – Taking the Next Step Into Depravity Michael hardly got any sleep that night. When he did his dreams were filled with images of Jenny and her large penis. He tossed and turned in frustration. As he rolled over for what felt like the thousandth time he was blinded by the s... Read full Story
Gwapo67 2022-05-13 5,297 Bareback Creampie Guy Fucks Shemale cum in mouth
50%
Lady Regina
I know that many say that I I’m a coward because I am comfortable living in the closet as a part time female and not expressing my special female side completely. My friends all tell me to go out and have fun and not worry about what people say or think. In spite of that, and because of the prudish... Read full Story
Regina10 2022-07-01 5,044 Crossdresser Big Tits Masturbation Bareback Fetish Blowjob Ladyboy gangbang Lingerie Guy Fucks Shemale Mature pov
100%
Shemale Fantasy
I had wanted to be with a she-male for some time. I had purchased several she-male DVDs and found that being with someone as sexy as that really turned me on. I would fantasize for hours on end about being with one of those 'special' girls. Several of my male lovers couldn't understand my attraction... Read full Story
shemale lover 2011-08-27 4,210 suck cum swallowing facefucking
50%
Giving Away Virginia Holton
Today would have to wait, thought Marla Holton as she hurriedly gathered her bag and notebook in preparation for a no-holds-barred departure from her office at Prism Design. As general manager she had the privilege of arriving and leaving at will, though no one could ever fault her for not putting i... Read full Story
shemale lover 2011-10-08 4,599 shemale cum ass fucking
0%
Sexing It Up
What catches your eye when you're viewing sample pornographic video clips on the Internet? When it comes to sex, my own tastes are eclectic, although I find myself watching videos involving anal sex, bisexual threesomes, cum shots, gay males, lesbians, oral sex, public nudity, shemales, and spank... Read full Story
shemale lover 2011-11-26 4,374 interracial sex spanking
87%
They Were Right
They were my friends, but I'd had sex with both of them. Not at the same time, but I had dated the one for a month and just started dating the other. So, although the thought had never crossed my mind before, I found myself dressed up as a girl for Halloween. After we had partied at a few clubs and ... Read full Story
shemale lover 2011-12-29 5,821 shemale Big Cock porn